Large group vacation rentals in South Bristol, ME

Cozy, private, and beautifully situated near the banks of the Damariscotta River, the Charming South Bristol Cottage offers the quintessential Maine experience in one of the Midcoast’s loveliest towns. In the same family since 1947, this home is a wonderful place to make memories, whether you’re curled up by the fire in the mornings and evenings, watching the waves crash at Pemaquid Point, walking in South Bristol and Christmas Cove, or picking up lobster fresh from the boats in town. It’s the way life should be! What’s nearby: South Bristol is a classic Maine town - an active lobstering village with friendly, welcoming people and stunning vistas. You’ll experience the relaxing intimacy of a small town with access to plenty of tourist sites and activities, including kayaking, hiking, fishing, charter boat tours, shopping, and dining close by. You can pick up incredibly fresh lobster at the South Bristol Fisherman’s Co-op half a mile east, take a dip in the brisk waters of Pemaquid Beach 11 miles east, or enjoy a beautiful day trip to Camden, Boothbay Harbor, or Monhegan Island. Things to know: Free WiFi Full kitchen

Come relax on this gorgeous slice of unspoiled Maine coast at this oceanfront cabin with multiple rocky beaches nearby. There is a deep water dock perfect for sunbathing, swimming, or fishing, and the cabin’s interior features a rustic, wood-paneled design with high rafters and an open living and dining space. You will enjoy modern amenities such as WiFi, TV, music, and plenty of fun games. There is one newly renovated bathroom with a cheery red floor, a pedestal sink, and a new shower. What’s nearby: There are many nearby trails that are part of the Boothbay Land Trust. A short drive brings you to downtown Boothbay Harbor, where you will find many fine restaurants and shops, a great aquarium, and the amazing Coastal Maine Botanical Gardens. Things to know: Free WiFi Full kitchen Coin laundry - laundromat in town

Paradise awaits at this beautiful, two-story home conveniently located on a dead-end street near the East Boothbay Village! This is the perfect spot to bring family and friends and experience a truly relaxing and memorable escapade. You will be a short three-mile drive from Boothbay Harbor, where numerous restaurants and marinas await. Discover amazing attractions within a short drive, including Boothbay Harbor Country Club, Coastal Maine Botanical Gardens, Maine State Aquarium, Chocolate Church Arts Center, Maine Maritime Museum, Pemaquid Beach Park, and Fisherman Museum. This splendid retreat boasts a beautifully decorated open floor plan that seamlessly combines all living spaces into one. Spread out comfortably in the living room, furnished with an extensive sofa, a wood stove, and a smart TV with streaming services to keep you entertained during your stay. When mealtime comes, put on the chef’s apron and prepare exquisite homemade meals for your crew in the well-appointed, open kitchen, complete with all the major appliances to whip up everything that comes to mind. The living area opens onto a screened porch offering impressive views of the Damariscotta River and a wonderful spot to dine alfresco. The adjoining open deck is also a fantastic spot to take in the marvelous river views. Another great perk is the access to a shared beach and dock at the residence, which are shared with 2-3 neighboring homes. Additional perks include a gas grill, a washer/dryer, high-speed WiFi, and a soaking tub. Things to Know Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. All guests shall abide by The Good Neighbor Policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises.

Pets Welcome w/ Fee | Cookout Ready | Near Public Kayak & Canoe Launches Nestled between Damariscotta River and Linekin Bay, this bright 3-bedroom, 2-bathroom home is perfect for rejuvenating waterfront adventures! Walk to the marina or take a short drive to the scenic Ocean Point Walk. Back at the vacation rental, unwind in the cozy living area or soak in stunning views of the Damariscotta River from the front porch. Your leisurely East Boothbay stay awaits! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed  - Bedroom 2: 1 queen bed - Bedroom 3: 1 queen bed, 1 lofted twin XL bed OUTDOOR LIVING  - Deck, outdoor dining table, rocking chairs, water views - Gas grill (seasonal) - Front porch INDOOR LIVING  - 4 Smart TVs - Board games, books - Kitchenette w/ microwave, refrigerator, sink - Dining table, breakfast bar - Chandeliers MAIN KITCHEN - Stove/oven, refrigerator, microwave - Keurig coffee maker, toaster - Dishware/flatware, cooking basics - Trash bags/paper towels GENERAL   - Free WiFi  - Mini-split air conditioning/heat - Linens/towels, hair dryer - Washer/dryer, iron/board - Keyless entry FAQ - Homeowner on-site (backyard cabin) - Pet fee (paid pre-trip) ACCESSIBILITY - 2-story home, step to enter  - Bedroom & full bathroom on 1st floor - Main living room & kitchen on 2nd floor PARKING - Driveway (3 vehicles) - Street parking -- THE LOCATION -- - Walk to general store - 4 miles to Ocean Point Walk - 20 miles to Pemaquid Point Lighthouse - 6 miles to Boothbay Railway Village Museum - 63 miles to Portland Int'l Jetport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome--because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $75 fee (+ fees & taxes) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story home requires a step to enter. The main living room and kitchen are located on the 2nd floor - A bedroom with a kitchenette and en-suite bathroom is located on the 1st floor and requires an exterior door to access - The homeowner may be on-site in a separate cabin located in the backyard, with the entrance facing away from the main property - The gas grill is available in the summer months Licence number: 0179

Newly Renovated In 2025. Linekin Bay Lookout is a private East Boothbay deckhouse set above Linekin Bay, where pines, tidewater, and sunset light define the stay. This 3-bedroom, 2-bath home pairs classic Maine warmth - vaulted wood ceilings, exposed beams, broad windows, and wood floors - with the simple pleasures guests come here for: coffee on the deck, seafood on the grill, and a private wooded path through the pines to the rocky tidal shore. The upstairs living level is the heart of the home. The living room looks out toward the bay and opens to the long second-floor deck, which connects the living area and primary bedroom. Gather under the vaulted ceiling, cook in the adjacent kitchen, linger over dinner by the glass doors, or, after a day on the water, step outside to watch the sun set over Linekin Bay. The home sleeps up to five guests. Upstairs, the primary bedroom has a king bed, deck access, bay views, a dressing area, and a newly updated bathroom with a tiled walk-in shower. Downstairs are two additional bedrooms - one queen and one double - plus a second updated full bath, laundry room, and family room, giving couples, small families, or friends on a quiet getaway room to gather and space to retreat. The setting feels secluded but still connected. Pick up freshly baked muffins or cinnamon buns from East Boothbay General Store just down the road, head into Boothbay Harbor for restaurants, shops, boat tours, whale watching, and harbor walks, or spend the day at Coastal Maine Botanical Gardens. Head to Ocean Point for classic coastal walks, salt-air views, ocean swims, and a glimpse of Ram Island Light, guarding the eastern entrance to Boothbay Harbor and the mouth of the Damariscotta River. ​​​​​​​Bigelow Laboratory is also within walking distance of the home, making Linekin Bay Lookout a practical and peaceful East Boothbay base for visiting scientists, researchers, public-event guests, seasonal staff, and others spending extended time in the region. With Wi-Fi, Ethernet, a dedicated workspace, and a quiet setting among the pines, the home is also well suited to remote work, writing, reflection, or a longer coastal stay. Good to know: The shoreline below the home is private, natural Maine coast - rocky and tidal rather than sandy. It is a beautiful place for tide-watching, rock-hopping, and quiet time by the water; water shoes are recommended for low-tide exploring.

Spread out between multiple sitting areas, a spacious kitchen, and three floors at this expansive 4BR/3.5BA East Boothbay home. Outdoors, a sprawling deck, gazebo, and gorgeous garden offers an outdoor haven for dining and sunny-day relaxation. The third floor also has a widow’s walk offering a view towards the ocean. Drive 10 minutes to Boothbay Harbor, the Coastal Maine Botanical Gardens, or 15 minutes to the Boothbay Harbor Country Club. You’re also under a 10-minute stroll to the acclaimed Carriage House Restaurant, offering a modern menu of New England-inspired dishes. ABOUT THE HOUSE There’s a fresh coastal feel throughout this stylish home, offering a relaxing home base after a day of outdoor fun. Curl up on the sectional sofa or cushioned chairs in the main sitting area. Opposite, a bookshelf contains an entertainment center with a 48’ flat screen TV. Steps away, chairs and couches furnish two additional sitting areas — perfect for group chit-chat and planning day trips. The chef in your group will love the large and contemporary kitchen, complete with a full suite of stainless steel appliances. The kitchen is a great social space too, with a central island seating three. Share sit-down meals around the eight-person dining table. A sprawling deck overlooking the garden boasts cushioned chairs and a six-person dining table for al fresco meals. A wooden walkway leads to a gazebo, where another dining table seats four. There’s also a gas grill for afternoon barbecues. The home is spread across three floors, with total sleeping space for 12 guests. On the entry-level, the master suite features two queen beds and ample storage space. Guests here have their own en-suite bathroom with a walk-in shower. Upstairs, garden views and a glimpse of the ocean await in a second bedroom featuring a king bed, two comfy chairs, and a private deck with a table seating two. An en-suite bathroom has a walk-in shower. A third bedroom offers the same impressive views, a plush queen bed, and a chaise lounge. The kid-friendly fourth bedroom comes with two twin-over-twin bunk beds. On the top floor, a bonus living/sleeping area offers the best ocean views in the house. A daybed (with a trundle beneath) and two sitting chairs furnish this tucked-away space. The house also has a guest bathroom with a tub/shower combination and a half bath. Extra amenities include complimentary Wi-Fi, cable TV, and a washer/dryer. Driveway parking is available for four cars. THE LOCATION This East Boothbay home overlooks Linekin Bay, with adjacent walking trails leading to Linekin and Burley Preserves. Just a 10-minute drive away, Boothbay Harbor offers boating, sailing and fishing trips. Head to Cap’n Fish and search for whales surfacing along the Maine coastline, or book trips aboard the Schooner Eastwind to visit the Burnt and Ram Island lighthouses. For a special evening meal, book a table at Carriage House Restaurant (an 8-minute walk) for craft cocktails and upscale New England comfort food.

Escape to a new and secluded cabin in the woods in charming Boothbay. This spacious 4BR/3BA home offers comfortable accommodations for your group of 15. Feel right at home in the open-concept living area with vaulted ceilings and warm wood paneling, and step out to a wraparound deck with open-air dining. Soak up rich maritime history in East Boothbay, or discover eclectic shopping and waterfront dining in Boothbay Harbor - both just minutes from your door. ABOUT THE CABIN The open-concept kitchen, living, and dining area is both spacious and cozy, with soaring ceilings and knotty pine paneling. Settle as a group onto the inviting sofas (one converts to a queen sleeper) and plush armchair to swap stories from the day’s adventures in Boothbay Harbor, or step out to a sprawling, wraparound deck with reclining lounge chairs, and open-air dining for seven. The second living area is configured with a queen sleeper sofa. Prepare family meals in the luxe kitchen with granite countertops and stainless steel appliances, including a French-door fridge. Or lend the chef a hand at a center island bar with seating for four. Bay windows lend sunlight and sophistication in the dining area, where a wood table is a lovely gathering spot for eight. BED & BATH The master suite boasts a king bed, twin sleeper chair, massive walk-in closet, sliding door access to the deck, a Peloton bike, and a TV. Get some work done at a wood writing desk, and refresh in the private en-suite bathroom with soaking tub and glass shower. Upstairs, find three additional bedrooms with full closets. The second guest room includes two twin beds and a twin trundle. The third bedroom has three twin beds. The fourth room is outfitted with a comfy queen bed. A guest bathroom on the main level features a shower and pedestal sink, while the second-floor bathroom has a tub/shower combination. EXTRA AMENITIES & DETAILS Your reservation at this wooded retreat includes complimentary Wi-Fi, a washer/dryer, and parking for four cars. Please note that a 4WD vehicle is required to access this property during the winter months. LOCATION Nestled in the trees on a quiet wooded lot, this secluded log cabin is ideally located just 10 minutes from the heart of Boothbay Harbor. Give the cook the night off and dine at Lobsterman’s Wharf, a casual seafood tavern with a waterview deck just a 5-minute walk away. Soak up maritime history in the village of East Boothbay with a rich shipbuilding heritage. Then, head to East Boothbay General Store for lunch fare and fresh baked goods.

An exceptional stay awaits at this tranquil vacation home. Tucked into the woods for privacy and just 1/2 mile from the water, this one-bedroom rental has everything you need for a relaxing getaway to Midcoast Maine. Relax and unwind on the wrap-around deck or fire up the gas grill for a backyard barbecue. Enjoy private access to the ocean via the association, with a dock, float, beach, and waterfront picnic area with beautiful views of Linekin Bay all just a half-mile from the home. Bright and inviting, the interior offers an open floor plan with strong natural lighting and all the comforts of home. The kitchen comes equipped with a full suite of stainless steel appliances, including a dishwasher, for easy home-cooking and stress-free cleanup. After the day’s adventures, cozy up in the living room and unwind with your favorite shows and movies on the smart TV. Modern must-haves include free WiFi. WHAT’S NEARBY A short drive into the town of Boothbay Harbor offers many local attractions, including the Opera House with live concerts, the Carousel Theater, whale watching, boat rides, harbor tours, trolley rides, kayaking outfitters, unique stores for shopping, and a great selection of local bars and dining, plus a movie theater and the Hannaford supermarket. The Boothbay Region Landtrust offers a wide variety of hiking trails on the local land preserves. Other favorite attractions are Southport and Hendrick’s Head beach, Lighthouses, Boothbay Railway Museum, Ocean Point scenic drive. Pemaquid Point Lighthouse and beach, Reid State Park, and Popham Beach are all an easy day trip away. Please check with our local Chamber of Commerce and the Boothbay Region Land Trust for everything this region has to offer.

Get ready to enjoy spectacular sunsets and peaceful nights at this warm and inviting beach house in the sought after Seawood Park Community in Bristol. Spread out over two well-appointed stories, this wonderful home features a well-equipped, full kitchen, two dining tables for meals, rainy day games, or laptops, and two distinct living areas. Step outside onto the first-floor deck and take in west-facing glimpses of Johns Bay and Rutherford Island. When you want to get out and explore, make your way to the nearby walking path that runs along the shoreline and leads to a private sand beach. THINGS TO KNOW Beach towels included.

Find nature right at your front door at this luxurious, dog- and family-friendly waterfront home. Watch for a pair of nesting eagles, seals lounging on the rocks each summer, and fishermen hauling lobster traps from the front deck each morning while you sip your coffee and enjoy the sunrise. If you’re looking for more urban charms, downtown Boothbay’s shops and restaurants are only three miles away. Outdoor space at home includes not only the lovely deck, but also a patio downstairs and a wide, waterfront lawn. Fire up the gas grill for a barbecue and spend evenings in the deck’s hot tub, admiring the stars. Gather around the firepit in the yard for some marshmallows or explore the water in one of the provided kayaks. Inside, you’ll find abundant natural light, cathedral ceilings, and a wall of deck-front windows that bring the view indoors. The gourmet kitchen features high-end appliances, including a wine fridge, and lots of gleaming countertops, including a huge kitchen island. Dine together at the adjacent table or pull up a barstool at the island to keep it casual. In the evening, grab one of the movie-theater-style reclining seats, get the floor-to-ceiling gas fireplace going, and host a family movie night in the living room. More entertainment options include a wet bar complete with a retro mini-fridge and popcorn machine, free high-speed WiFi, cable, five streaming-capable TVs, board games, a pool table, and an air hockey table. At the end of the night, tuck the kids into one of the fun bunk rooms and have one last soak in the hot tub - another perfect vacation day awaits tomorrow. THINGS TO KNOW Streaming services are available with guest accounts.

Set back on a grassy knoll overlooking the water, this 3BR/2BA Boothbay Harbor home offers a truly tranquil vacation retreat. Drive minutes to restaurants, hiking trails, whale watching, and the quaint fishing village of Boothbay Harbor. Sleeps 10. INSIDE THE HOUSE After arriving in this leafy neighborhood overlooking the water, pull up outside the house on a driveway with parking space for 4. A dark wood walkway leads up to the front door. As you step inside, turn right into the main living room – an open-concept space with hardwood floors and lots of natural light. There’s seating for 6 on a charcoal gray couch and sofa chair. After a day of coastal adventures, curl up for the evening in front of a 40” flat-screen TV. Next to the living area, a dining area with a glass top table seats 6. From here, gain access to a wrap-around back deck with a BBQ grill and outdoor seating overlooking the trees. Next to the dining table, an open kitchen makes it easy to chat with the group while prepping meals. Find plenty of appliances close to hand, including an electric stove-oven combo, microwave, and dishwasher. In the mornings, fire up the coffee maker or whizz up fruit smoothies in the kitchen blender. A hallway off the living area leads to a bathroom with a single-sink vanity and shower/tub combo. Further along, you’ll find the primary bedroom, furnished with a queen bed and 32” TV. Next door, a snug 2nd living room offers an extra hang-out space with an L-shaped couch and 42” TV with cable. The remaining bedrooms are located upstairs. On the left of the stairs, a bedroom has 2 queen beds, while the 3rd bedroom comes with a queen bed and two twin beds. Both bedrooms also share access to a bathroom with a shower/tub combination. LOCATION Drive 4 minutes down the coast to East Boothbay. Stroll around the marina in the morning, then grab a lunchtime bite at East Boothbay General Store or Lobsterman’s Wharf Restaurant. Take a 7-minute drive for beautiful coastal views at Ocean Point, or watch the waves roll in against the rocky beach at Grimes Cove. Just 12 minutes away, the fishing village of Boothbay Harbor is a tranquil place to wander between laid-back cafes, shops, bars, and eateries. Grab brunch at Mama D’s, try the Lobster Dock for seafood, then stroll to Downeast Ice Cream for a sweet treat. The harbor is also a great jumping off point for whale watching, fishing trips, and island sailing tours, the perfect way to soak up the natural beauty surrounding this quaint coastal town. Enjoy Boothbay’s Coastal Maine Botanical Gardens! If you’re planning a trip in November or December plan on experiencing Gardens Aglow, Maine’s largest light display, with over 360,000 LED lights illuminating the central gardens and buildings.

Cute and comfortable, this quiet cottage built in 1800 offers a peaceful escape for those in search of a tranquil Boothbay Harbor experience. Unplug and appreciate the surroundings in the warmth of the sunroom. The living room includes more blankets, additional seating, and a resituated pull-out couch for optimal lounging as you watch TV. Enjoy a peaceful night’s rest on the California King bed in the main bedroom, just updated in December 2024. Need some quiet time? Enjoy the separate bunkhouse that has been converted into a comfortable, relaxing space with a library. The Lobster Trap, a three-season (spring, summer, and fall) garage hangout space, features cozy blankets, an electric fireplace, a couch, a custom bar with bar stools, a Fire TV, and a full-sized refrigerator. For fun, try the ping-pong table, the dartboard, the deluxe Scrabble board, or a game of Hook 21. The yoga mat is perfect for winding down, as are the L.L. Bean rocking chairs. Take a walk through the neighborhood on your way to the beach at Barrett Park. The cottage is located on 1.5 acres giving it a secluded feel. There are also great outdoor spaces, including two lawns for the kids to play on, a firepit location with Adirondack chairs and new solar lighting for family gatherings, a propane grill, and many lawn games included with the property. Indulge in grilled meals on the new custom-built picnic table. There is very little light pollution on the property so the stars are beautiful if you are interested in stargazing. When it’s time to call it a night, take refuge in the primary bedroom and turn on the electric fireplace for a cozy ambience as you drift to sleep. This home sits within walking distance of Barrett Park (three-quarters of a mile south), where you can have a scenic picnic or swim in the waters of Lewis Cove. Downtown Boothbay Harbor is one mile west across the footbridge, home to beautiful marinas, fantastic restaurants, and charming shops. The area immediately surrounding town is similarly full of activities. It is also less than three miles from the Boothbay Harbor Country Club. Take the kids to the Maine State Aquarium, located four miles west. The Coastal Maine Botanical Gardens are also just four miles away, where you can walk the trails to view 250 acres of manicured gardens and natural landscape. This home has been the epitome of a coastal Maine home for over 222 years. The charm and solid construction is both timeless and enduring. You’ll enjoy the cottage and all that the Boothbay Harbor area offers during your stay. THINGS TO KNOW Streaming services are available with guests’ own account(s). Guests can enjoy access to books, card games, puzzles for indoor fun, cornhole boards, a football, a soccer ball, and a Frisbee for outdoor fun. This home lies along the summer trolley route, which is free of charge and will bring you around Boothbay Harbor.

Welcome to your perfect getaway in Boothbay, ME! This newly built, charming home is designed for family-friendly fun and relaxation. Step onto the spacious deck, complete with patio furniture and a gas grill, ideal for enjoying warm summer evenings. After a day of exploring the beautiful coastal scenery, unwind in the hot tub while soaking in the serene surroundings. Inside, discover a newly equipped kitchen with modern appliances—fridge, stove, oven, and microwave—making meal preparation effortless. The cozy living room invites family gatherings, featuring a TV with cable for entertainment. Comfortable sleeping arrangements are provided to ensure a restful stay for all. Conveniently located just steps from the ocean and a short distance to town, you’ll have easy access to local restaurants, shops, and attractions. Enjoy bird watching, scenic drives, and hiking amidst Boothbay’s stunning autumn foliage. Equipped with amenities like WiFi and a washer/dryer, this home ensures a comfortable and relaxing stay. Book your visit today and create unforgettable memories in this beautiful coastal retreat!

Find the storied charms of Midcoast Maine at this Boothbay Harbor property, a bay view cottage and adjoining newly renovated (2023) two-story apartment with a spacious deck. With two separate living spaces, families or groups that wish to travel with one another can still have the privacy they desire. Built in 1936 near the tip of Wall Point. Quietly nestled in the woods of Wall Point, this property includes a summer cottage and a garage apartment on the other side of the deck. Take afternoon strolls to the beach at Barrett Park one mile west, and grab lobster rolls for lunch in bustling Boothbay Harbor two miles west. Revel in the Linekin Bay views as the sea breeze brushes your face from this serene property. Overlook and Seaview are also only 1.2 miles away from the center of Booth. Spend your mornings kayaking, hiking, and jogging on the surrounding country roads, and return home to relax in the comfortable living space. Inside, you’ll find all the creature comforts and conveniences you need during your stay, such as both homes including a fully-equipped kitchen. The outside area includes a grill, picnic table, and chairs in case you’d prefer to sear your meals. After dining, read the newspaper beneath the cathedral ceilings, and toss your clothes in the washer/dryer as you use the fast WiFi to make plans for the day ahead or take advantage of the smart TVs to watch something on your favorite apps. Take a leisurely drive to the Coastal Maine Botanical Gardens five miles northwest, and pick up lunch at Boothbay Lobster Wharf on the way home. Soak in the sunshine as you dine out on the deck, feel the cool coastal breezes from Linekin Bay across the street, and spend the evening curled up by the wood-burning fireplace. Discover the simple allures of life on the coast of Maine - begin planning your getaway to Boothbay Harbor today! THINGS TO KNOW This vacation rental is not equipped with air-conditioning.

Retreat into the romance of coastal Maine at this exquisite Boothbay Harbor vacation rental that bursts with vintage character and seaside charm. Your harbor-view gem comprises two separate three-level homes. You’ll love the antique decor and original 1800s wood floors, while modern amenities include updated kitchens and smart TVs. Across the street, you’ll find sunset chairs with the best footbridge view in town. Stroll to the pier, waterfront parks, and tasty dining options. Pack your binoculars for Cap’n Fish’s Whale Watching, climb aboard the Windjammer Eastwind, or rent a seafaring vessel at Schooner Eastward. Boothbay Harbor Country Club and Coastal Maine Botanical Gardens are within a short drive. Captain’s Quarters’ modern living area presents a Sonos system and a large 4K smart TV with access to Netflix, Hulu, Apple TV, and all of today’s online entertainment. Prepare delicious dishes in the convenient full kitchen, configured with a small eat-in table and a larger nearby dining table. Sleep soundly in the primary suite that has an en suite bathroom that is also accessible via the hallway. One of the guest bedrooms includes a telescope for harbor gazing. All bedrooms provide a smart TV, bedside USB charging, and a Bluetooth music system. Head of the Harbor has an inviting living area with twin and queen sofa beds. The 4K smart TV provides access to Netflix, Hulu, Apple TV, and other services. A large farmhouse sink and an eat-in table highlight the beautifully updated kitchen. The gas grill on the deck is perfect for sunny afternoon cookouts. The bedroom occupies the entire top floor and features a charming antechamber with a window air-conditioning unit. Extra perks include complimentary commercial-grade WiFi and a backup generator. Each home is equipped with a private washer/dryer. THINGS TO KNOW The homes are not directly connected.

You’ll be able to walk to the beach at Barrett Park, the footbridge, and the very heart of downtown Boothbay Harbor from this polished, dog-friendly home. Whether you choose to spend your days kayaking, whale-watching, or hiking, you’ll find that you’re just where you want to be. This family home is spread out across two levels, with hardwood floors and free WiFi throughout. As you enter, you’ll be greeted by a billiard room to the left and a living room to the right, where you can pile on the leather sofas, watch Netflix on TV, and play board games well into the evening. The light-filled, well-equipped kitchen is just beyond, offering stainless steel appliances, an eat-in dining table, and sliding doors that lead outside to the new composite deck, firepit, and gas grill. After a barbecue dinner and a walk around the neighborhood with your dogs, you can come home to toss the day’s clothes in the washer/dryer. There’s one bedroom on the main floor and two bedrooms upstairs - including a special room for the kids with chalkboards on the wall. Additional perks include ample parking. Things to Know Please note that dogs must be leashed and cleaned up after; there are foxes in the area. Dogs are not allowed to sleep on beds, but a dog bed is provided.

Captain’s Quarters | Historic Coastal Luxury in the Heart of Boothbay Harbor Experience the perfect blend of historic New England charm and modern luxury at Captain’s Quarters, a beautifully restored 1800s cottage nestled in the heart of Boothbay Harbor. Overlooking the iconic footbridge and located directly across from the harbor, this elegant retreat offers a front-row seat to one of Maine’s most beloved coastal destinations. Step outside and immerse yourself in the vibrant harbor atmosphere. Downtown shops, restaurants, galleries, and waterfront attractions are just a short stroll away. Enjoy a leisurely brunch at a local favorite, indulge in a relaxing spa treatment nearby, or take in the spectacular harbor sunsets from the Adirondack chairs located across the street. For adventure seekers, golf courses, sailing excursions, whale-watching tours, harbor cruises, and boat rentals are all within easy reach. Inside, the home seamlessly combines classic architecture with contemporary comforts. The inviting living area is designed for relaxation, featuring comfortable furnishings, a Sonos sound system, and a 55-inch 4K Smart TV with access to Netflix, Hulu, Apple TV, and other popular streaming services. The well-appointed kitchen makes meal preparation a pleasure, offering modern appliances, ample workspace, and a dishwasher for easy cleanup. Guests may also enjoy the shared outdoor patio area with a gas grill, perfect for casual summer cookouts. Spanning three levels, each bedroom is thoughtfully equipped with its own Smart TV, Bluetooth music system, and convenient USB charging stations. The primary suite offers a peaceful retreat with access to a private en-suite bathroom. One guest bedroom even features a telescope, allowing guests to enjoy harbor views and stargazing from the comfort of the home. Additional amenities include: Central air conditioning Commercial-grade high-speed WiFi Washer and dryer Sonos whole-home audio system Backup generator Smart TVs throughout the home Whether you’re exploring the waterfront, setting sail on the harbor, enjoying fresh Maine seafood, or simply relaxing while watching boats pass by, Captain’s Quarters offers an unforgettable Boothbay Harbor experience. Things to Know This vacation rental is accessed by two steep flights of stairs and may not be suitable for guests with mobility limitations. The outdoor gas grill and patio area are shared with neighboring guests. Convenient walking access to downtown Boothbay Harbor, waterfront attractions, dining, shopping, and excursion departures.

You’ll be wonderfully located near the best of Boothbay Harbor at this home just across the footbridge from downtown. Enjoy fantastic access to Barrett Park and the Boothbay Lobster Wharf mere steps away. This home makes an enviable home base in Boothbay Harbor, whether planning to spend your days whale-watching, kayaking with Tidal Transit Kayak, or simply perusing the shops, restaurants, and galleries that populate this darling Midcoast town. After a day of coastal excursions, you’ll return to a casual, comfortable living area with two sofas and a smart TV, a well-appointed kitchen with all the essentials, and a small indoor dining space. Right out back are a small deck with outdoor seating and marshland views, a gas grill for summer barbecues, and a picnic table where you can gather for lobster rolls and haddock pulled straight from the ocean. There are cornhole and croquet games available for use as well! THINGS TO KNOW This home is the ground level of a duplex.

Full of sunlight, ocean breezes, and gorgeous views of Lobster Cove, this oceanfront apartment is a beautiful home base for taking in the beauty of Boothbay Harbor. With Barrett Park right next door and the footbridge within walking distance, you’ll have excellent access to the ocean shore and downtown shops, galleries, and restaurants. This apartment sits on a waterfront piece of property that it shares with a main house. Walk home from a day spent gallery-hopping in town to be greeted by a front deck overlooking the cove - a lovely spot for sharing lobster rolls from Boothbay Lobster Wharf down the street. Inside, find an open living space lined with windows and such at-home comforts as window air-conditioning and high-speed WiFi. There’s a kitchen with every essential, an indoor dining table, and a streaming-capable TV for your evening entertainment. In the evenings, when you’re not dining out, enjoy a gas grill and a propane firepit with a view of the water, which is shared with guests in the main house. THINGS TO KNOW Streaming services are available with guests’ accounts. There is no washer/dryer. Elevators are not available. Must use stairs to get to the second floor.

2 Mi to Cap'n Fish's Whale Watch | Cozy Wood-Burning Fireplace Craving an escape where water adventures meet laid-back living? This Boothbay Harbor vacation rental cabin in Sprucewold delivers a true taste of Maine! Spend beach days swimming and tide pooling, fire up the grill for sunset feasts on the deck, and browse the village’s renowned art galleries just down the street. With 2 bedrooms, 1 bath, and all the essentials, this home is perfect for couples or small groups looking to explore! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 2 twin beds INDOOR LIVING - Flat-screen TV - Dining table, sofa seating - Remote-controlled gas fireplace OUTDOOR LIVING - Deck, outdoor dining - Gas grill - Front porch KITCHEN - Refrigerator, stove/oven, microwave - Cooking basics, dishware & flatware - Drip coffee maker, toaster GENERAL - Free WiFi - Mini-split A/C & heating units - Linens/towels, complimentary toiletries - Hair dryer ACCESSIBILITY - Single-story cabin, 5 steps to enter PARKING - Gravel driveway (4 vehicles) ADDT’L ACCOMMODATIONS - There is an additional property available down the street with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking -- THE LOCATION -- - 2 miles to Lobster Cove Preserve - 2 miles to Sweet Action Charters - 4 miles to Maine State Aquarium - 5 miles to Gregory Hiking Trail - 62 miles to Portland International Jetport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story cabin requires 5 steps to enter

The best of downtown Boothbay Harbor is a short walk away from Boothbay Cottage, a 3BR/2BA home. Original accents pay homage to the home’s coastal history, while a sparkling kitchen with stainless steel appliances creates modern convenience. In the evenings, make use of the gas grill or relax by the wood-burning firepit in the backyard. In addition to beloved downtown restaurants, Bayside Cottage also keeps you close to the Coastal Maine Botanical Gardens, riverside fishings spots, and ocean-adventure boat charters. Take a 10-minute stroll into town over the Harbor Footbridge. A plush sofa set invites you to unwind in the living area. The flat-screen TV with Roku allows you to log in to your preferred streaming services. Complimentary board games provide additional entertainment options. Stainless steel appliances and sleek soapstone countertops bring modern style and upscale utility to the kitchen. When you’re ready to eat, gather around the table for seven in the dining area. This home sleeps seven guests in three bedrooms. Sleep soundly on a queen-size bed in the primary suite. The en-suite bathroom is configured with a walk-in shower. The second bedroom holds a queen-size bed, whereas the third bedroom is furnished with a full-size bed and a twin-size bed. The guest bathroom includes a tub/shower combination. Prepare tasty meals on the patio’s gas grill. Take a reflective stroll through the backyard and enjoy the relaxing coastal breeze. On clear nights, roast marshmallows over the wood-burning firepit. Extra perks include complimentary Wi-Fi and a private washer/dryer. Things to know: * This home has seasonal window AC units * All guests shall abide by The Good Neighbor Policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. * No smoking is permitted anywhere on the premises. * The backyard is shared with an adjacent property, with each property having its own seating area, fire pit, and grill. * This two-story home has step-free access from the driveway.

** Temporary alert: if you are booking in June please note that the dock will not be in till July. ** Nestled in the charming coastal town of East Boothbay, this picturesque oceanfront cottage offers a serene retreat with breathtaking views of the Atlantic. The cozy living room features a decorative fireplace that, while non-functional, creates a warm ambiance perfect for cool coastal evenings. This well-appointed cottage includes two comfortable queen beds for restful nights and a range of modern amenities, including a washer/dryer and a fully equipped kitchen. Step outside to the spacious deck furnished with patio seating and a BBQ grill, where you can relax and take in sweeping ocean views. Whether enjoying a morning coffee or cooking in the kitchen, the tranquil ocean vistas provide a constant, soothing backdrop. A private dock and float allow for easy access to the water, perfect for sailing, stand-up paddleboarding, kayaking, or just enjoying a swim. Whale-watching tours, winery visits, hiking trails, and deep-sea fishing excursions are all nearby, offering something for every adventurer. After a day of exploration, unwind with a shower or simply savor the stunning waterfront setting. Conveniently located near local restaurants, shops, and attractions, this oceanfront cottage is the ideal base for exploring all East Boothbay has to offer. Whether you’re seeking a peaceful retreat or an active seaside getaway, this cottage provides the perfect setting for a memorable coastal Maine vacation. Book your stay today and experience the beauty of the ocean up close! Things to Know

This newly remodeled home is the epitome of charm. The hues of pink and blue, the floral prints, the wicker woven sofa frame - it all works together to paint the picture of a serene, idyllic vacation home. Enjoy water views of Linnekin Bay from this serene and quiet property nestled in the woods of Wall Point. The living room gets wonderful light and sea breezes with multiple bay facing windows and French doors. The kitchen will, likewise, transport you back to simpler times. It is well-equipped for any vacation cooking needs. The large furnished deck is the perfect place to hang with the whole group. Grill food and dine al fresco, or gather wood for the firepit and enjoy a cool evening by the fire. This home also welcomes dogs, so every member of the family can come along and enjoy the fun. Don’t forget to take advantage of the fast WiFi as well as the smart TV to connect and enjoy all of your favorite TV apps. Seaview is within one and a half miles away from the center of Boothbay Harbor where you can find a variety of unique shops, restaurants, coffee shops, fishing charters, harbor cruises, whale watches, and more! You are just a short walk from the Lobster Cove Preserve, which has hiking trails, and Barrets Park, which welcomes dogs. THINGS TO KNOW This home is not equipped with air-conditioning. This home is a subunit of Sea View. Sea View Main can be rented separately.

Enjoy elevated water views of the open ocean, Linekin Bay, and two lighthouses from this classic Ocean Point cottage. The ocean views cannot be beat as you enjoy them straight from the large, open living area. The wood-burning fireplace will keep you warm on those cooler nights, and you’ll still be able to hear the sound of the crashing waves while you play board games or read one of the provided books. There is also a full kitchen for easy meal preparation, a furnished patio with a gas grill, and plenty of space for dining and relaxing indoors and outdoors. Located right on the water, you may never want to leave this home’s gorgeous vistas, but if you venture out, you’ll find the Ocean Point Preserve just a half-mile away. The town center is less than four miles away, where you’ll find plenty of shops, restaurants, and entertainment. THINGS TO KNOW The home has been upgraded with additional heat pumps which provide cooling and heating throughout the entire cottage.